Silafunctional compounds in organic synthesis. 32. Stereoselective halogenolysis of alkenylsilanes: stereochemical dependence on the coordination state of the …

…, M Akita, K Maeda, M Kumada

Index: Tamao, Kohei; Akita, Munetaka; Maeda, Kimio; Kumada, Makoto Journal of Organic Chemistry, 1987 , vol. 52, # 6 p. 1100 - 1106

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Citation Number: 58

Abstract

Halogenation of (E)-1-octenyltrimethylsilane (l),-trifluorosilane (2), and-pentafluorosilicate (2- )(3) by iodine chloride, bromine, and N-bromosuccinimide has been examined in nonpolar solvents, mostly carbon tetrachloride, and in polar solvents, mostly dimethylformamide, in the dark. Cleavage reactions of 1 proceed uniformly with inversion of configuration to form (2)-1-octenyl halides, while 3 is cleaved with retention of configuration to form (E)-1- ...